Hydrochloric Acid → 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid

HRID 610473

반응식

HRID 610473 반응식
[CH3:1][C:2]1[O:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N:3]=1.[N-:13]=[N+:14]=[N-:15].[Na+].[OH-].[Na+].Cl>C(O)(=O)C>[CH3:1][C:2]1[N:3]([C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]([OH:7])=[O:8])[N:15]=[N:14][N:13]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3회HCID 33557Sodium AzideHCID 68236Acetanthranil

생성물 1

HCID 125241922-(5-methyl-1H-tetrazol-1-yl)benzoic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
27.5 °C

실험 절차

The crude 2-methyl-4-oxo-3,1-benzoxazine was dissolved in acetic acid (1.9 L). Sodium azide (130.0 g) was added to the solution in portions with stirring. The reaction mixture was cooled in an ice bath to maintain the reaction temperature at 25 to 30° C. during the addition. The reaction mixture was allowed to stir at ambient temperature over the weekend. The acetic acid was removed under vacuum to provide a white solid. The solid was combined with 10% sodium hydroxide (1.4 L) then heated on a steam bath for 1 hour. Additional sodium hydroxide (120 g of 50% sodium hydroxide) was added. The mixture was heated on a steam bath for an additional hour then allowed to cool to ambient temperature overnight. Additional sodium hydroxide (120 g of 50% sodium hydroxide) was added. The mixture was heated on a steam bath for 2 hours then allowed to cool. The reaction mixture was poured with rapid stirring into a mixture of concentrated hydrochloric acid (1.0 L) and ice (3 L). The resulting mixture was stirred at ambient temperature overnight. A precipitate was isolated by filtration, rinsed with water then slurried with water (4 L). The solid was isolated by filtration, rinsed with water then oven dried at 50° C. to provide 278.0 g of crude 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid as a tan solid, m.p. 157-160° C. The crude material was dissolved in 10% sodium hydroxide (2.5 L). The resulting solution was heated (95-99° C.) for 2.5 hours, cooled, then poured with vigorous stirring into a mixture of concentrated hydrochloric acid (500 mL) and ice (5 L). The resulting mixture was allowed to stir for 2 hours. The precipitate was isolated by filtration, rinsed with water, then slurried with water (3 L). The solid was isolated by filtration, rinsed with water then dried overnight at ambient temperature to provide 228 g of 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid, m.p. 164-166° C.

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionduring the addition
  3. stirringto stir at ambient temperature over the weekend
  4. customThe acetic acid was removed under vacuum
  5. customto provide a white solid
  6. temperaturethen heated on a steam bath for 1 hour
  7. temperatureThe mixture was heated on a steam bath for an additional hour
  8. temperatureto cool to ambient temperature overnight
  9. temperatureThe mixture was heated on a steam bath for 2 hours
  10. temperatureto cool
  11. additionThe reaction mixture was poured
  12. stirringThe resulting mixture was stirred at ambient temperature overnight
  13. customA precipitate was isolated by filtration
  14. washrinsed with water
  15. customThe solid was isolated by filtration
  16. washrinsed with water
  17. customoven dried at 50° C.

출처 및 근거

ORD 기록
ord-9a6ce5250593432daa4223069ecfc1db
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998619

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